Iodine → 4-Iodo-6-methoxynicotinonitrile

HRID 56719

반응식

HRID 56719 반응식
C([N-]C(C)C)(C)C.[Li+].[CH3:9][O:10][C:11]1[N:16]=[CH:15][C:14]([C:17]#[N:18])=[CH:13][CH:12]=1.[I:19]I.[Cl-].[NH4+]>C1COCC1.C(OCC)(=O)C>[I:19][C:13]1[CH:12]=[C:11]([O:10][CH3:9])[N:16]=[CH:15][C:14]=1[C:17]#[N:18]

참가 물질

7

반응물 4

HCID 807IodineHCID 25517Ammonium ChlorideHCID 2724682Lithium diisopropylamideHCID 27367762-Methoxy-5-pyridinecarbonitrile

생성물 1

HCID 1176054124-Iodo-6-methoxynicotinonitrile

시약·촉매·용매 2

HCID 8028Tetrahydrofuran용매2회HCID 8857Ethyl Acetate용매

반응 조건

온도
-78 °C

실험 절차

At −78° C., 19.4 ml of lithium diisopropylamide (2 molar in THF/heptane/ethylbenzene, 1.3 eq.) were added to a solution of 4.0 g (29.8 mmol) of 6-methoxypyridine-3-carbonitrile in 120 ml of THF, and the mixture was stirred at −78° C. for 1 h. At −78° C., a solution of 9.1 g (35.8 mmol) of iodine in 20 ml of THF was then added, and the reaction mixture was stirred at −78° C. for 1 h and then carefully added to saturated aqueous ammonium chloride solution. After addition of ethyl acetate, the reaction mixture was extracted three times with ethyl acetate. The combined organic phases were dried (magnesium sulphate), filtered and concentrated under reduced pressure. The crude product was purified by flash chromatography (silica gel 60, mobile phase: cyclohexane/ethyl acetate mixtures). Yield: 4.0 g (purity 92%, 48% of theory)

후처리

  1. stirringthe reaction mixture was stirred at −78° C. for 1 h
  2. extractionthe reaction mixture was extracted three times with ethyl acetate
  3. dry with materialThe combined organic phases were dried (magnesium sulphate)
  4. filtrationfiltered
  5. concentrationconcentrated under reduced pressure
  6. customThe crude product was purified by flash chromatography (silica gel 60, mobile phase: cyclohexane/ethyl acetate mixtures)

출처 및 근거

ORD 기록
ord-7152e453c2da495a95d1b2cf28d7baa1
출처 데이터셋
uspto-grants-2016_09
특허 번호
US09434690B2

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